ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL 1,2-DIOLS VIA N-BOC OXAZOLIDINES

被引：30

作者：

AGAMI, C

COUTY, F

LEQUESNE, C

机构：

[1] Laboratoire de Chimie Organique Associé au CNRS, Université Pierre et Marie Curie, 75005 Paris

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)76893-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoisomerically pure N-Boc 2-acyloxazolidines were synthesized from phenylglyoxal and ethyl glyoxylate. Reaction of these heterocycles with Grignard reagents is highly stereoselective. Homochiral 1,2-diols were ultimately obtained after N-deprotection, hydrolysis and reduction of the intermediate alpha-hydroxy aldehyde. The asymmetric induction can be explained by a chelated model.

引用

页码：3309 / 3312

页数：4

共 30 条

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